When I moved to New York City, I took a sales job out of necessity, thinking I would find a way back to an editorial position once my wife and I settled in. Eight years later, I still find myself miserable and mired in ad sales. What careers are there for people like myself looking to escape sales?

You are only trapped by the walls you build around yourself, grasshopper. (Sorry, I was watching a kung fu movie last night). I can’t tell if your complaints are about sales in general or your particular experience, but I can tell you this: The whole media landscape has changed, and you can’t separate the business side from the content side any longer. Sales is like the circulatory system, delivering oxygen to the vital organs — so you can do anything with a background in sales, including marketing or a more content-focused role. Consider exploring opportunities in multi platform sales. Digital sales talent is critical for cracking the monetization of the online content business model, which is an exciting new frontier.

I’m in my 50s and just can’t keep up with all of the new technology at work. My employer started a reverse-mentoring program where junior staffers my kids’ age are helping senior staff understand technology better. Will I look like a dinosaur if I participate?

You will look like a dinosaur if you keep referring to social media as “the Twitter.” And you say “50s” like the next stop for you is a nursing home. If your employer has set up the program, then presumably they’ve made it safe for getting those less familiar with current technology up to speed so they don’t become extinct. But if you don’t want anyone to discover just how technology-challenged you are, then it isn’t difficult to get up to speed outside of work on your own. Heck, even one of your kids, for that matter. However you do it, just make sure you learn enough to understand common technology terms and usage — and don’t embarrass yourself talking about “the cloud” as a forecast for possible rain.